We're now on Day 5 of the 12 Days of Christmas and the fifth skill in our countdown of what fundraisers need for fundraising in the new year.

So far, we've covered:

1) Curiosity

2) Grounded Confidence

3) Discernment (wow, that one really resonated!)

4) Data & Tech Literacy

And that brings us to #5 - sing it with me now - FIVE GOLDEN R . . er, I mean, "SYSTEMS THI-I-INK-ING" . . . ok, so it doesn't scan exactly right, but you get it and you're welcome for the earworm. Brief re-cap if you're just joining us, rather than talking about projections and what MIGHT happen, we're focusing on things you, dear fundraiser, can control - skills you can focus on and develop to be prepared for whatever comes, regardless of what projections or prognostications say.

Ever feel like instead of fundraising, you’re playing whack-a-mole and hoping something sticks?

You fix one thing and another pops up. You address that, and a third thing appears. You solve the new problem, only to discover the original one has quietly returned, slightly worse and wearing a fake mustache.

At some point, it stops feeling like strategy and starts feeling like chaos and goals feel like a great idea, sure, but knows if we'll get there or not.

Please welcome Systems Thinking to the chat.

What We Mean by "Systems Thinking"

Let's start with a definition of what a System really is:

from Introduction to Systems Thinking by Daniel H. Kim

A System is just a bunch of things that affect one another while trying to do something. The key is that they're interrelated and dependent upon each other to form the whole.

Oh, sure, those things can - and do! - work independent of each other, but combined they exist to achieve a goal or carry out a clear function.

Which means every fundraising operation — large or small, sophisticated or scrappy — is already a System. The only question is whether it’s one you’ve designed intentionally or one you’re reacting to in real time.

Whack-a-mole fundraising is what happens when you don’t realize you’re operating inside one.

Characteristics of a System

Daniel Kim also defines the key characteristics of a System, i.e., optimal Systems all include the following:

1. Systems have a Purpose (raise money);

2. All parts must be present for a system to carry out its purpose optimally (the key is "optimally" - yes, you can raise major gifts without a clear case-for-support (storytelling), but it's a LOT harder);

3. Systems attempt to maintain stability through feedback (metrics, dashboards, data - not the board chair's spouse who doesn't like the branding)

Why Tactics Start Misbehaving

Most fundraisers don’t set out to ignore systems. They set out to solve problems.

Major gifts aren’t growing, so you hire a major gift officer. Or buy wealth screening or a prospect list. The annual fund feels flat, so you add urgency. An event underperforms, so you add a new sponsorship level. Data feels unreliable, so you buy a new tool.

All reasonable responses.

And then things get . . . weird.

The major gift officer can’t find qualified prospects. Urgency bumps short-term revenue but donor fatigue creeps in. The event makes money but exhausts staff and volunteers. The new system creates cleaner reports and messier workflows.

None of these moves are wrong. They’re just incomplete.

Because no tactic stands alone.

Major Gifts Don’t Exist In Isolation (But We Talk About Them That Way)

Take major gifts, since they’re top of mind for a lot of organizations right now.

Major gifts don’t simply appear because you hired the right person or adopted the right model. They emerge from an ecosystem that includes the annual fund, data integrity, prospect research, stewardship practices, donor experience, internal expectations, and time (among other things).

If the annual fund isn’t healthy, the pipeline is thin. If the data is messy, research is guesswork. If stewardship is inconsistent, trust erodes. If leadership wants quick wins, relationships get rushed.

You can push harder on any one of those pieces, but the pressure doesn’t disappear. It just moves.

That’s systems thinking showing up, whether you invited it or not.

Events Are Systems Too (Even When We Treat Them Like Line Items)

Events are another great example.

An event might look successful on paper — good gross revenue, solid attendance — while quietly draining energy from every other part of the system.

Staff are exhausted, volunteers stretched thin, major gift follow-up gets delayed, and the Annual Fund messaging gets sidelined.

When someone says, “The event worked,” the systems thinker asks, “At what cost, and to what else?”

That’s not being negative. It’s being honest.

Why Whack-A-Mole Feels Endless

Without Systems Thinking, every problem feels like the most immediate issue - so we throw additional tactics at it to fix it. In the short-term.

Low response rates? Re-write the email or letter. Revenue flat? Add another appeal. Staff burnout? Do more with less. Need more major gifts? Find "better" "wealthier" people/Mackenzie Scott/Oprah, etc.

Each response makes sense in isolation. But isolation is the problem.

Systems Thinking, conversely, asks us to view the pattern as a whole and identify how the entirety of it informs the specifics or tactics.

Low response rates?

• What's the quality of our data? What appeals did perform well? What story are we telling? Of those that responded before, who received appropriate and quality stewardship? All of those things could affect response.

Revenue flat?

• What's our response rate? Have we changed case-for-support/are we really describing impact? Is it flat right now or overall for the year? Are there external circumstances? Have we increased ask amounts? Are fewer donors giving or did we lose a specific funder/grant/etc.?

Staff burnout?

• Do they have the resources they need? Have there been unaddressed performance issues? Is the dang copier broken again? Have they taken any time off recently? If not, what can we do to re-shuffle workload so they can take their PTO? Who else is putting pressure on them from other areas?

Need more major gifts?

• Have we reviewed our lapsed, LYBUNT, and SYBUNT lists? Who are our most frequent/most loyal donors? What does our data tell us about response over time - 5 years, 10 years. What donors have upgraded and/or downgraded? Are we explaining impact and story well enough? What does our stewardship look like? Have we invested in donor relations?

Systems Thinking shifts “How do we fix this particular thing?” and starts asking, “What’s reinforcing this pattern?”

Often, the thing you’re trying to solve today is a downstream effect of a decision made months or years ago. More urgency. Less reflection. More volume. Fewer handoffs. Cleaner reports. Messier experiences.

You’re not bad at your job, you’re just working inside a system that’s doing exactly what it was designed to do.

Or, as James Clear (author of Atomic Habits) puts it:

This Isn't About Control; It's About Coherence

Here’s an important distinction.

Systems Thinking is not about controlling every variable. Humans are involved. Chaos is baked in.

Systems Thinking is about coherence.

Do your strategy, systems, story, and daily behavior actually support one another? Or are they quietly pulling in different directions?

When things are incoherent, work feels harder than it should. Results feel unpredictable. People compensate for broken processes. Donors feel mixed messages even when they can’t quite articulate why.

When things are coherent, effort travels further. Small changes matter more. People trust the process, not just the outcome.

That’s not magic. It’s alignment.

Data Problems Are Often System Problems In Disguise

This is where data management sneaks in.

Organizations often say they have a “data problem,” when what they really have is a system problem.

Data is inconsistent because processes are inconsistent. Reports are confusing because definitions aren’t shared. Dashboards don’t help because no one agrees on what decisions they’re meant to inform.

Buying a new tool doesn’t fix that. Neither does blaming the CRM.

Systems Thinking asks different questions. Who enters the data? Why? At what point? For whose use? What decisions depend on it? What happens when it’s wrong?

Until those questions are answered, data will keep popping up as the next mole.

Systems Thinking Is Also A Care Practice

Poorly designed systems don’t just produce inefficient results. They produce human fallout.

Fundraisers burn out because urgency is constant and relief never arrives. Donors feel pressured because every lever is pulled at once. Staff absorb friction that should have been designed out.

Good systems don’t eliminate hard work. They reduce unnecessary harm.

They make it easier for people to do good work without constantly compensating for invisible breakdowns.

How Fundraisers Actually Develop Systems Thinking

Not by drawing elaborate diagrams or by learning new jargon or purchasing the next Bright Shiny Object (BSO).

Not by investing in "AI Optimization" (the current BSO; I said what I said.)

Systems Thinking develops slowly, through attention and intention.

You start noticing where pressure shows up. You track problems upstream instead of reacting downstream. You ask what a fix might improve — and what it might strain. You get more comfortable naming tradeoffs out loud. You resist optimizing the loudest problem without asking what it’s connected to.

Over time, you stop playing whack-a-mole.

Not because problems disappear, but because you understand why they appear where they do.

The single greatest way to develop the skill of Systems Thinking is, first, recognizing that everything is part of a System. Then, secondly, when a mole arises, rather than simply whacking it, asking the hard questions of what caused it to pop up, what other things will be affected if you simply whack it away, and unraveling the threads that tie everything together to identify where the kink in the hose actually is. (You might also want to invest in addressing mixed metaphors, but I digress and that might be a 'me problem.')

Systems Thinking Is The Skill That Ties The Whole Series Together

Curiosity helps you see more clearly. Grounded Confidence helps you trust yourself. Discernment helps you choose among options. Data and tech literacy help you interpret inputs.

Systems Thinking is what helps all of those skills work together, instead of at cross-purposes.

It doesn’t give you one right answer.

It gives you relief from the feeling that everything is broken all the time.

And that’s a pretty good place to be.